[go: up one dir, main page]

WO2010008299A1 - Nouveaux lipides contenant du soufre pour utilisation en tant que supplément alimentaire ou médicament - Google Patents

Nouveaux lipides contenant du soufre pour utilisation en tant que supplément alimentaire ou médicament Download PDF

Info

Publication number
WO2010008299A1
WO2010008299A1 PCT/NO2009/000262 NO2009000262W WO2010008299A1 WO 2010008299 A1 WO2010008299 A1 WO 2010008299A1 NO 2009000262 W NO2009000262 W NO 2009000262W WO 2010008299 A1 WO2010008299 A1 WO 2010008299A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
lipid compound
compound according
lipid
prevention
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/NO2009/000262
Other languages
English (en)
Inventor
Anne Kristin Holmeide
Ragnar Hovland
Morten Braendvang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pronova Biopharma Norge AS
Original Assignee
Pronova Biopharma Norge AS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40419454&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2010008299(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to ES09798181.5T priority Critical patent/ES2573977T3/es
Priority to US13/054,212 priority patent/US8759558B2/en
Priority to UAA201101386A priority patent/UA109252C2/ru
Priority to NZ590645A priority patent/NZ590645A/xx
Priority to BRPI0916456A priority patent/BRPI0916456B8/pt
Priority to MA33613A priority patent/MA33083B1/fr
Priority to KR1020177020879A priority patent/KR101901836B1/ko
Priority to HRP20160557TT priority patent/HRP20160557T1/hr
Priority to EP09798181.5A priority patent/EP2313090B1/fr
Priority to DK09798181.5T priority patent/DK2313090T3/en
Priority to AU2009271791A priority patent/AU2009271791B2/en
Application filed by Pronova Biopharma Norge AS filed Critical Pronova Biopharma Norge AS
Priority to CN200980136136.2A priority patent/CN102159200B/zh
Priority to MX2011000556A priority patent/MX2011000556A/es
Priority to CA2730958A priority patent/CA2730958C/fr
Priority to HK12101390.0A priority patent/HK1161078B/xx
Priority to EA201170193A priority patent/EA022593B1/ru
Priority to JP2011518677A priority patent/JP5628164B2/ja
Publication of WO2010008299A1 publication Critical patent/WO2010008299A1/fr
Anticipated expiration legal-status Critical
Priority to IL210673A priority patent/IL210673A/en
Priority to ZA2011/00666A priority patent/ZA201100666B/en
Priority to US14/263,793 priority patent/US20140316002A1/en
Priority to US15/040,260 priority patent/US20170029368A1/en
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
    • A61K31/10—Sulfides; Sulfoxides; Sulfones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C313/02—Sulfinic acids; Derivatives thereof
    • C07C313/04—Sulfinic acids; Esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/54—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/55—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/61—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

Definitions

  • Novel sulphur containing lipids for use as food supplement or as medicament
  • the present invention relates to lipid compounds of the general formula (I):
  • R 1 is selected from a C10-C22 alkyl, a C10-C22 alkenyl having 1-6 double bonds, and a C10-C22 alkynyl having 1-6 triple bonds;
  • R 2 and R 3 are the same or different and may be selected from a group of substituents consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group, provided that R 2 and R 3 cannot both be a hydrogen atom; or
  • R 2 and R 3 can be connected in order to form a cycloalkane like cyclopropane, cyclobutane, cyclopentane or cyclohexane;
  • Y is selected from sulphur, sulfoxide, and sulfone
  • X represents a carboxylic acid or a derivative thereof, a carboxylic ester or a carboxamide
  • the compounds of formula (I) are capable of existing in stereoisomeric forms. It will be understood that the invention encompasses all optical isomers of the compounds of formula (I) and mixtures thereof.
  • the invention also relates to pharmaceutical compositions and lipid compositions comprising such compounds, and to such compounds for use as medicaments or for use in therapy, in particular for the treatment of diseases related to the cardiovascular, metabolic and inflammatory disease area.
  • dietary polyunsaturated fatty acids have been shown to regulate plasma lipid levels, cardiovascular and immune functions, insulin action, and neuronal development and visual function.
  • Tetradecylthioacetic acid is a modified fatty acid which has a number of powerful effects demonstrable both in-vivo and in-vitro.
  • TTA has properties very similar to natural fatty acids, the main difference being that it cannot be oxidised by the mitochondrial ⁇ -oxidation, but significantly increases the oxidation of other fatty acids. Despite the fact that TTA is not able to undergo ⁇ -oxidation, it is metabolised in most ways as a normal saturated fatty acid.
  • TTA affects oxidative status at different levels by having the potential of changing the antioxidant defence system, in addition to being an antioxidant itself through its free radical scavenging capacity.
  • TTA may prevent the oxidative modification of low-density lipoprotein (LDL) particles in plasma and reduce the generation of lipid peroxides.
  • LDL low-density lipoprotein
  • novel fatty acid derivatives represented by the general formula (I) have higher affinities for the receptors PPAR ⁇ and PPAR ⁇ compared to TTA and (all-Z)-3-thia-6,9,12,15-octadecatetraenoic acid.
  • Fatty acid derivatives represented by the general formula (I) also reduced triglycerid, cholesterol and free fatty acids levels in a dyslipidemic mice model to a greater extent than TTA and (all-Z)-3-thia-6,9,12,15-octadecatetraenoic acid.
  • One object of the present invention is to provide lipid compounds having improved biological activity compared to 3-thia fatty acids. This object is achieved by a lipid compound of formula (I)
  • Ri is selected from a C1 0 -C 22 alkyl, a C 10 -C 2 2 alkenyl having 1-6 double bonds, and a C10-C22 alkynyl having 1-6 triple bonds;
  • R 2 and R 3 are the same or different and may be selected from a group of substituents consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group, provided that R 2 and R 3 cannot both be a hydrogen atom; or
  • R 2 and R 3 can be connected in order to form a cycloalkane like cyclopropane, cyclobutane, cyclopentane or cyclohexane; • Y is selected from sulphur, sulfoxide, and sulfone;
  • X represents a carboxylic acid or a derivative thereof, a carboxylic ester or a carboxamide
  • said alkyl group may be selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and n-hexyl; said alkenyl group may be selected from the group consisting of allyl, 2- butenyl, and 3-hexenyl; said alkynyl group may be selected from the group consisting of propargyl, 2-butynyl, and 3-hexynyl; said halogen atom may be selected from the group consisting of fluorine, chlorine, bromine, and iodine; said alkoxy group may be selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, sec- butoxy, phenoxy, benzyloxy, OCH 2 CF 3 , and OCH 2 CH 2 OCH 3 ; said acyloxy group may be selected from acetoxy, propionoxy, and butyl;
  • one of the substituents R 2 and R 3 of the compound of formula (I) is hydrogen and the other one is selected from a group of substituents consisting of a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group.
  • R 2 and R 3 are independently selected from a hydrogen atom, an alkyl group, an alkoxy group or an aryl group; or R 2 and R 3 can be connected in order to form a cycloalkane.
  • R 2 and R 3 are independently selected from a hydrogen atom, an alkyl group, or a methoxy group or an ethoxy group.
  • R 2 and R 3 are independently selected from a hydrogen atom, an ethyl, methoxy or ethoxy group, phenyl; or R 2 and R 3 are connected to form a cyclobutane group.
  • the substituents R 2 and R 3 of the compound of formula (I) are the same or different and may be selected from a group of substituents consisting of a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group.
  • R 2 and R 3 are alkyl groups selected from methyl, ethyl, n-propyl, or isopropyl, more preferably selected from methy or ethyl, and most prebreably R 2 and R 3 are ethyl.
  • the substituent Ri of the compound of formula (I) is a Ci O -C 22 alkyl, and the said compound is derived from a saturated fatty acid.
  • the substituents R 2 and R 3 of the compound of formula (I) are the same or different and may be selected from a group of substituents as mentioned above, and the substituent Ri is a Ci O -C 22 alkyl, and the said compound is derived from a saturated fatty acid.
  • Ri When derived from a polyunsaturated fatty acid, Ri is typically a Ci O -C 22 alkenyl with 2-6 double bonds, e.g 3-6 double bounds, e.g. 3-6 methylene interrupted double bonds in Z configuration.
  • Ri is:
  • Ri may be a C10-C22 alkynyl, e.g. a C16-C22 alkynyl with 1-6 triple bonds.
  • the substituent Y of the compound of formula (I) is sulfur.
  • the substituent Y of the compound of formula (I) is sulfoxide.
  • the substituent Y of the compound of formula (I) is sulfone.
  • the substituent X of the compound of formula (I) is a carboxylic acid in the form of an ester, a free acid, a triglyceride or a phospholipid.
  • the substituent X is a carboxylic acid in the form of an ester, or a free acid, and more preferably X is a carboxylic acid in the form of a free acid.
  • the substituent Ri is a C 10 -C 22 alkyl, and the lipid compound being derived from a saturated fatty acid;
  • R 2 and R 3 are the same or different and may be selected from a group of substituents consisting of a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group; preferably R 2 and R 3 are alkyl groups; and X is a carboxylic acid in the form of a free acid.
  • the invention also relates to salts of the compound of formula (I). Such salts may be represented by
  • Z + is selected from the group consisting of Li + , Na + , K + , NH/,
  • X COO "
  • Z 2+ is selected from the group consisting of Mg 2+ , Ca 2+ ,
  • the compounds of formula (I) are capable of existing in stereoisomers forms. It will be understood that the invention encompasses all optical isomers of the compounds of formula (I) and mixtures thereof. Hence, compounds of formula (I) being present as diastereomers, racemates and enantiomers are included.
  • the compound of formula (I) is ethyl 2-((5Z,8Z, 11 Z, 14Z, 17Z)-icosa-5,8, 11 ,14,17-pentaenylthio)butanoate.
  • the present invention also relates to a lipid compound according of formula (I) for use as a medicament.
  • the present invention provides a food supplement, a food additive, or a neutraceutical preparation comprising a lipid compound of formula (I).
  • a food supplement may be produced for administration through any route of administration.
  • the food supplement may be administered as a liquid nutritional or as a beverage.
  • the food supplement may be in the form of a capsule, e.g. a gelatine capsule, and the capsule may be flavoured.
  • the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a compound of formula (I), preferably together with one or more pharmaceutically acceptable carriers or excipients.
  • the novel lipid compounds and compositions of the invention may be formulated in conventional oral administration forms, e.g. tablets, coated tablets, capsules, powders, granulates, solutions, dispersions, suspensions, syrups, emulsions, sprays, etc using conventional excipients, e.g.
  • compositions may likewise be administered by conventional administration routes, i.e. orally.
  • orally administrable compositions e.g. tablets, coated tablets, capsules, syrups, etc is especially preferred.
  • a suitable daily dosage of the compound according to formula (I) is 1 mg to 10 g of said compound; 50 mg to 1 g of said compound, or 50 mg to 200 mg of said compound.
  • the pharmaceutical composition according to the invention may be used as a medicament.
  • the present invention also relates to lipid composition
  • lipid composition comprising a lipid compound according to formula (I).
  • lipid compound according to formula (I)
  • at least 60% by weight, or at least 80% by weight of the lipid composition is comprised of said compound.
  • the lipid composition may further comprise a pharmaceutically acceptable antioxidant, e.g. tocopherol.
  • a pharmaceutically acceptable antioxidant e.g. tocopherol.
  • the present invention relates to a lipid composition for use as a medicament.
  • the present invention relates to the use of a lipid compound according to formula (I) for use in: • activation or modulation of at least one of the human peroxisome proliferator- activated receptor (PPAR) isoforms ⁇ , Y or ⁇ , wherein said compound e.g. is a pan-agonist or modulator
  • PPAR peroxisome proliferator- activated receptor
  • HMG hypertriglyceridemia
  • NAFLD non-alcoholic fatty liver disease
  • the invention also relates to lipid compounds according to formula (I) for the treatment of the above mentioned conditions, and to methods for the treatment and/or prevention of the conditions listed above, comprising administering to a mammal in need thereof a pharmaceutically active amount of a compound according to formula (I).
  • the present invention encompasses methods for manufacturing lipid compounds according to formula (I).
  • the raw material may e.g. originate from a vegetable, a microbial and/or an animal source, such as a marine fish oil.
  • a marine oil or a krill oil is used.
  • lipid compound relates to fatty acid analogues derived from e.g. saturated fatty acids, monounsaturated fatty acids, polyunsaturated fatty acids and lipids comprising 1-6 triple bonds.
  • a "pharmaceutically active amount” relates to an amount that will lead to the desired pharmacological and/or therapeutic effects, i.e. an amount of the combination product which is effective to achieve its intended purpose. While individual patient needs may vary, determination of optimal ranges for effective amounts of the combination product is within the skill of the art. Generally, the dosage regimen for treating a condition with the combination product of this invention is selected in accordance with a variety of factors, including the type, age, weight, sex, diet and medical condition of the patient.
  • a pharmaceutical composition is meant a lipid compound according to the invention in any form suitable to be used for a medical purpose.
  • Treatment includes any therapeutic application that can benefit a human or non-human mammal. Both human and veterinary treatments are within the scope of the present invention. Treatment may be in respect of an existing condition or it may be prophylactic. Nomenclature and terminology
  • Fatty acids are straight chain hydrocarbons possessing a carboxyl (COOH) group at one end ( ⁇ ) and (usually) a methyl group at the other ( ⁇ ) end. In chemistry, the numbering of the carbon atoms starts from the ⁇ end.
  • the ⁇ carbon refers to the first carbon after the carbon that attaches to the functional group, and the second carbon is the ⁇ carbon.
  • methylene interrupted double bonds relates to the case when a methylene group is located between to separate double bonds in a carbon chain of a lipid compound.
  • the inventors have surprisingly found that the following lipid compound shown in categories A-E, are particularly preferable.
  • Ri is a C10-C22 alkyl
  • X represents a carboxylic acid or a derivative thereof, a carboxylic ester or a carboxamide
  • Category B • derived from monounsaturated fatty acids •
  • Ri is a C1 0 -C22 alkenyl having 1 double bond X represents a carboxylic acid or a derivative thereof, a carboxylic ester or a carboxamide
  • Category C derived from polyunsaturated fatty acids
  • Ri is a C 10 -C 22 alkenyl having 2-6 double bonds
  • X represents a carboxylic acid or a derivative thereof, a carboxylic ester or a carboxamide
  • R 1 C 22 with 6 methylene interrupted double bonds in Z-configuration
  • Y S
  • Ri C 18 with 5 methylene interrupted double bonds in Z-configuration
  • Y S
  • Ri is a C10-C22 alkynyl
  • X represents a carboxylic acid or a derivative thereof, a carboxylic ester or a carboxamide
  • Ri is selected from a C10-C 22 alkyl, a C1 0 -C22 alkenyl having 1-6 double bonds, and a C1 0 -C22 alkynyl having 1-6 triple bonds
  • X represents a carboxylic acid or a derivative thereof, a carboxylic ester or a carboxamide
  • Y is sulfoxide or sulfone
  • lipid compounds according to the invention are:
  • Ri C 20 H 31
  • R 2 ethyl
  • R 3 a hydrogen atom
  • Y S
  • X a carboxylic acid in the form of a triglyceride
  • R 1 C 20 H 3 I
  • Y SO 2
  • X COOH
  • the compounds of categories A-E above were R 2 and R 3 are different, are capable of existing in stereoisomeric forms, i.e. all optical isomers of the compounds and mixtures thereof are encompassed. Hence, the said compounds may be present as diastereomers, racemates and enantiomers.
  • Step IV IXL .
  • Step V _ X S ⁇ X
  • n 1 or 2
  • the alcohols described in method I and Il may be prepared directly from the carboxylic esters of, for example, naturally occurring fatty acids; e.g. alpha-linolenic acid, conjugated linoleic acid, eicosapentaenoic acid (EPA), etc. by reduction with a reducing agent like lithium aluminiumhydride or diisobultylaluminiumhydride at -10 to 0 0 C.
  • the alcohols can also be prepared by degradation of the polyunsaturated fatty acids EPA and DHA, as described by Holmeide et al. (J.Chem. Soc, Perkin Trans. 1 , 2000, 2271 ). In this case one can start with purified EPA or DHA, but it is also possible to start with fish oil containing EPA and DHA in mixture.
  • the leaving group (LG) present in compounds of formula (Xl) may, for example, be mesylate, tosylate or a suitable halogen, such as bromine.
  • the resulting alcohols can be converted, using functional group interconversion, by methods familiar to persons skilled in the art (step I), to compounds where the terminal hydroxy group have been transformed into a suitable leaving group (LG).
  • Suitable leaving groups include bromine, mesylate and tosylate.
  • the alcohols can be converted to the corresponding thiols (step IV) by methods familiar to persons skilled in the art.
  • the thiols can then be reacted further (step V) in a substitution reaction with compounds of formula (Xl), in the presence of base in an appropriate solvent system.
  • oxidising agents are m-chloro-perbenzoic acid (MCPBA), hydrogen peroxide (H 2 O 2 ) and oxone (potassium peroxymonosulfate).
  • an esterifying group such as a methyl of an ethyl group may be removed, for example, by alkaline hydrolysis using a base such as an alkali metal hydroxide, for example LiOH, NaOH or KOH or by using an organic base, for example Et 3 N together with an inorganic salt, for example LiCI in an appropriate solvent system.
  • a te/f-butyl group may be removed, for example, by treatment with an acid, for example an organic acid such as trifluoroacetic acid or formic acid in an appropriate solvent system.
  • An arylmethyl group such as a benzyl group may be removed, for example, by hydrogenation over a catalyst such as palladium-on-carbon in an appropriate solvent system.
  • the compounds of formula (I) wherein X is a carboxylic acid and in the form of a phospholipid can be prepared through the following processes.
  • GPC sn-glycero-3-phosphocholine
  • an activated fatty acid such as fatty acid imidazolides
  • Sn-Glycero-3- phosphocholine, as cadmium (II) adduct can also be reacted with the imidazolide activated fatty acid in the presence of DBU (1 ,8-diazabicyclo[5.4.0]undec-7-ene) to prepare the phosphatidylcholine of the respective fatty acid (International application number PCT/GB2003/002582).
  • Enzymatic transphosphatidylation can effect the transformation of phosphatidylcholine to phosphatidyletanolamine (Wang et al, J. Am. Chem. Soc, 1993, 115, 10487).
  • Phospholipids may also be prepared by enzymatic esterification and transesterification of phospholipids or enzymatic transphosphatidylation of phospholipids. (Hosokawa, J.Am. Oil Chem. Soc. 1995, 1287, Lilja-Hallberg, Biocatalysis, 1994, 195).
  • the compounds of formula (I) wherein X is a carboxylic acid in the form of a triglyceride can be prepared through the following process. Excess of the fatty acid can be coupled to glycerol using dimethylaminopyridine (DMAP) and 2-(1 H- benzotriazol-1-yl)-N,N,N',N'-tetramethyluroniumhexafluorophosphate (HBTU).
  • DMAP dimethylaminopyridine
  • HBTU 2-(1 H- benzotriazol-1-yl)-N,N,N',N'-tetramethyluroniumhexafluorophosphate
  • the compounds of formula (I) wherein X is a carboxylic acid in the form of a diglyceride can be prepared by reaction of the fatty acid (2 equivalents) with glycerol (1 equivalent) in the presence of 1.S-dicyclohexylcarbondiimide (DCC) and 4- dimethylaminopyridine (DMAP).
  • DCC 1.S-dicyclohexylcarbondiimide
  • DMAP 4- dimethylaminopyridine
  • the compounds of formula (I) wherein X is a carboxylic acid and in the form of a monoglyceride can be prepared through the following processes.
  • DMAP in chloroform gives a monodienoylglycerol.
  • Deprotection of the isopropylidene group can be done by treating the protected glycerol with an acidic (HCI, acetic acid etc.) (O'Brian, J.Org.Chem., 1996, 5914).
  • One method utilizes esterification of the fatty acid with glycidol in the presence of 1-(3-dimethylaminopropyl)-3- ethylcarbodiimidehydrochloride (EDC) and 4-dimethylaminopyridine (DMAP) to produce a glycidyl derivative.
  • EDC 1-(3-dimethylaminopropyl)-3- ethylcarbodiimidehydrochloride
  • DMAP 4-dimethylaminopyridine
  • TFAA trifluoroacetic anhydride
  • a 1 ,3-regiospecific lipase from the fungus Mucor miehei can be used to produce triglycerides or diglycerides from polyunsaturated fatty acids and glycerol.
  • a different lipase, the non-regiospecific yeast lipase from Candida antartica is highly efficient in generating triglycerides from polyunsaturated fatty acids (Haraldsson, Pharmazie, 2000, 3).
  • NMR nuclear magnetic resonance
  • Triphenylphosphine (PPh 3 ) (41.7 g, 159 mmol) was dissolved in dry tetrahydrofurane (THF) (250 ml_) at 0 0 C under inert atmosphere and added diisopropyl azodicarboxylate (DIAD) (30.8 ml_, 159 mmol). The mixture was stirred at 0 0 C for 40 minutes and then dropwise added a solution of (all-Z)-3,6,9,12- pentadecatetraenol (17.5 g, 79.4 mmol) and thioacetic acid (11.4 ml_, 159 mmol) in dry THF (150 ml_).
  • THF dry tetrahydrofurane
  • DIAD diisopropyl azodicarboxylate
  • Example 2 Preparation of (3Z,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraene-1 -thiol.
  • LiAIH 4 (2.05 g, 54.1 mmol) was suspended in dry diethyl ether (100 ml_) at 0 0 C under inert atmosphere. To this suspension was added dropwise a solution of S-
  • Triphenylphosphine (21.0 g, 80 mmol) was dissolved in dry THF (170 ml_) at 0 0 C under inert atmosphere and added DIAD (15.8 ml_, 80 mmol) dropwise. After 40 minutes at 0 0 C the white suspension was added dropwise to a solution of (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11 ,14,17-pentaen-1-ol (11.5 g, 40 mmol) and thioacetic acid (5.7 mL, 80 mmol) in dry THF (50 mL) during 15 minutes. The resulting turbid mixture was stirred at 0 0 C for 30 minutes, followed by ambient temperature for 1.5 hour.
  • Example 12 Preparation of ethyl 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11 ,14,17- pentaenylthio)propanoate (32).
  • the assay was carried out in-vitro in three stable reporter cell lines, PPAR ⁇ , PPAR ⁇ or PPARY, expressing respectively a chimeric protein containing the ligand binding domain (LBD) of human PPAR ⁇ , human PPAR ⁇ or human PPARy fused to the yeast transactivator GAL4 DNA binding domain (DBD).
  • LBD ligand binding domain
  • DBD yeast transactivator GAL4 DNA binding domain
  • the luciferase (Luc) reporter gene is driven by a pentamer of the GAL4 recognition sequence in front of a ⁇ -globin promoter.
  • the use of GAL4-PPAR ⁇ , GAL4-PPAR ⁇ and GAL4-PPAR ⁇ chimeric receptors allows for elimination of background activity from endogenous receptors and quantitation of relative activity across the three PPAR subtypes with the same reporter gene.
  • the PPAR selectivity of the substances was determined by comparison to known drug references (1 ⁇ M GW7647 for PPAR ⁇ , 1 ⁇ M L-165041 for PPAR ⁇ and 1 ⁇ M BRL49653 for PPARy) set of 100 % activity.
  • the assay was carried out in-vitro using mammalian-one-hybrid assays (M1H) comprising GAL4-DNA binding domain-PPAR ⁇ -LBD fusion constructs in conjunction with 5xGAL4-sites driven Photinus pyralis luciferase reporter construct in transiently transfected HEK293 cells.
  • M1H mammalian-one-hybrid assays
  • Compound (12) and positive control GW7647 were tested at different concentrations. The results are presented in Table 1.
  • This animal model has proven to be representative for the human situation regarding plasma lipoprotein levels, lipoprotein profiles, its responsiveness to hypolipidemic drugs (like statins, fibrates etc.) and nutrition.
  • hypolipidemic drugs like statins, fibrates etc.
  • APOE*3l_eiden mice develop atherosclerotic lesions in the aorta resembling those found in humans with respect to cellular composition and morphological and immunohistochemical characteristics.
  • Female APOE*3Leiden mice were put on a semi-synthetic Western-type diet
  • the test substances were administered orally as admix to the Western-type diet.
  • sunflower oil was added to a total oil volume of 10 mL/kg diet.
  • mice were fasted overnight (o/n) and blood samples were taken to measure plasma ketone bodies and free fatty acids.
  • blood samples were taken after a 4 hour-fast period to measure plasma cholesterol and triglycerides.
  • Ob/ob mice can be used as a model for type Il diabetes.
  • the mice are homozygous for the obese spontaneous mutation (Lep ob ) leading to leptin deficiency.
  • ob/ob mice may reach three times the normal body weight of wild type controls
  • ob/ob mice exhibit a diabetes type ll-like syndrome of hyperglycemia, glucose intolerance, elevated plasma insulin, infertility, impaired wound healing, and an increase in hormone production from both pituitary and adrenal glands.
  • All compounds were administered orally as admix to AM Il diet.
  • sunflower oil was added to a total oil volume of 10 ml/kg diet.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Mycology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicinal Preparation (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

La présente invention porte sur des composés lipidiques selon la formule générale (I) : (I) dans laquelle R1 est choisi parmi un alkyle en C10-C22, un alcényle en C10-C22 ayant 1 à 6 doubles liaisons et un alcynyle en C10-C22 ayant 1 à 6 triples liaisons; R2 et R3 sont identiques ou différents et peuvent être choisis dans un groupe de différents substituants; Y est choisi parmi sulfure, sulfoxyde et sulfone; et X représente un acide carboxylique ou un dérivé de celui-ci, un ester carboxylique, un anhydre carboxylique ou un carboxamide; ou un sel pharmaceutiquement acceptable, complexe ou solvate de ceux-ci. L'invention porte également sur des compositions pharmaceutiques et sur des compositions lipidiques comprenant de tels composés, et sur de tels composés pour utilisation en tant que médicaments ou pour une utilisation en thérapie, en particulier pour le traitement de maladies relatives au domaine des maladies cardiovasculaires, métaboliques et inflammatoires.
PCT/NO2009/000262 2008-07-15 2009-07-13 Nouveaux lipides contenant du soufre pour utilisation en tant que supplément alimentaire ou médicament Ceased WO2010008299A1 (fr)

Priority Applications (21)

Application Number Priority Date Filing Date Title
JP2011518677A JP5628164B2 (ja) 2008-07-15 2009-07-13 補助食品としてまたは薬剤として使用するための新規硫黄含有脂質
CN200980136136.2A CN102159200B (zh) 2008-07-15 2009-07-13 用作食品补充剂或药物的新的含硫脂质
UAA201101386A UA109252C2 (uk) 2008-07-15 2009-07-13 Сірковмісні ліпіди для застосування як харчових добавок або медикаментів
NZ590645A NZ590645A (en) 2008-07-15 2009-07-13 Novel sulphur containing lipids for use as food supplement or as medicament
BRPI0916456A BRPI0916456B8 (pt) 2008-07-15 2009-07-13 compostos lipídicos, composições de suplemento alimentar, farmacêuticas e lipídicas, método para produção de compostos lipídicos e uso de compostos lipídicos
MA33613A MA33083B1 (fr) 2008-07-15 2009-07-13 Nouveaux lipides contenant du soufre pour utilisation en tant que supplément alimentaire ou médicament
KR1020177020879A KR101901836B1 (ko) 2008-07-15 2009-07-13 식품 첨가물 또는 약제로 사용되는 신규 황 함유 지질
HRP20160557TT HRP20160557T1 (hr) 2008-07-15 2009-07-13 Novi lipidi koji sadrže sumpor za uporabu kao dodatak prehrani ili kao lijek
EP09798181.5A EP2313090B1 (fr) 2008-07-15 2009-07-13 Nouveaux lipides contenant du soufre pour utilisation en tant que supplément alimentaire ou médicament
US13/054,212 US8759558B2 (en) 2008-07-15 2009-07-13 Sulphur containing lipids for use as food supplement or as medicament
AU2009271791A AU2009271791B2 (en) 2008-07-15 2009-07-13 Novel sulphur containing lipids for use as food supplement or as medicament
ES09798181.5T ES2573977T3 (es) 2008-07-15 2009-07-13 Lípidos novedosos que contienen azufre para su uso como complemento alimenticio o como medicamento
CA2730958A CA2730958C (fr) 2008-07-15 2009-07-13 Nouveaux lipides contenant du soufre pour utilisation en tant que supplement alimentaire ou medicament
DK09798181.5T DK2313090T3 (en) 2008-07-15 2009-07-13 Novel sulphur containing lipids for use as food supplements or medicine
MX2011000556A MX2011000556A (es) 2008-07-15 2009-07-13 Nuevos lipidos que contienen azufre para el uso como suplemento alimenticio o como medicamento.
HK12101390.0A HK1161078B (en) 2008-07-15 2009-07-13 Novel sulphur containing lipids for use as food supplement or as medicament
EA201170193A EA022593B1 (ru) 2008-07-15 2009-07-13 Содержащие серу липиды для применения в качестве пищевой добавки или в качестве лекарственного средства
IL210673A IL210673A (en) 2008-07-15 2011-01-16 Fats, supplements and preparations containing them and their uses
ZA2011/00666A ZA201100666B (en) 2008-07-15 2011-01-26 Novel sulphur containing lipids for use as food supplement or as medicament
US14/263,793 US20140316002A1 (en) 2008-07-15 2014-04-28 Novel sulphur containing lipids for use as food supplement or as medicament
US15/040,260 US20170029368A1 (en) 2008-07-15 2016-02-10 Novel sulphur containing lipids for use as food supplement or as medicament

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US8080408P 2008-07-15 2008-07-15
US61/080,804 2008-07-15
EP08160450.6 2008-07-15
EP08160450A EP2147910A1 (fr) 2008-07-15 2008-07-15 Nouveaux composés lipidiques

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US13/054,212 A-371-Of-International US8759558B2 (en) 2008-07-15 2009-07-13 Sulphur containing lipids for use as food supplement or as medicament
US14/263,793 Continuation US20140316002A1 (en) 2008-07-15 2014-04-28 Novel sulphur containing lipids for use as food supplement or as medicament

Publications (1)

Publication Number Publication Date
WO2010008299A1 true WO2010008299A1 (fr) 2010-01-21

Family

ID=40419454

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NO2009/000262 Ceased WO2010008299A1 (fr) 2008-07-15 2009-07-13 Nouveaux lipides contenant du soufre pour utilisation en tant que supplément alimentaire ou médicament

Country Status (28)

Country Link
US (3) US8759558B2 (fr)
EP (2) EP2147910A1 (fr)
JP (1) JP5628164B2 (fr)
KR (2) KR20110031497A (fr)
CN (1) CN102159200B (fr)
AU (1) AU2009271791B2 (fr)
BR (1) BRPI0916456B8 (fr)
CA (1) CA2730958C (fr)
CL (2) CL2011000090A1 (fr)
CO (1) CO6341548A2 (fr)
DK (1) DK2313090T3 (fr)
EA (1) EA022593B1 (fr)
ES (1) ES2573977T3 (fr)
HR (1) HRP20160557T1 (fr)
HU (1) HUE029195T2 (fr)
IL (1) IL210673A (fr)
IN (1) IN2011CH01039A (fr)
MA (1) MA33083B1 (fr)
MX (1) MX2011000556A (fr)
MY (1) MY153620A (fr)
NZ (2) NZ601501A (fr)
PH (1) PH12011500113A1 (fr)
PL (1) PL2313090T3 (fr)
SG (1) SG192525A1 (fr)
UA (1) UA109252C2 (fr)
VN (1) VN28144A1 (fr)
WO (1) WO2010008299A1 (fr)
ZA (1) ZA201100666B (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011146873A1 (fr) * 2010-05-21 2011-11-24 Miller Brewing International, Inc. Préparation d'acides de houblon et de leurs dérivés
WO2011161030A1 (fr) 2010-06-21 2011-12-29 Sanofi Dérivés de méthoxyphényle à substitution hétérocyclique par un groupe oxo, leur procédé de production et leur utilisation comme modulateurs du récepteur gpr40
WO2012004269A1 (fr) 2010-07-05 2012-01-12 Sanofi Dérivés d'acide ( 2 -aryloxy -acétylamino) - phényl - propionique, procédé de production et utilisation comme médicament
WO2012004270A1 (fr) 2010-07-05 2012-01-12 Sanofi Dérivés 1,3-propanedioxyde à substitution spirocyclique, procédé de préparation et utilisation comme médicament
WO2012010413A1 (fr) 2010-07-05 2012-01-26 Sanofi Acides hydroxy-phényl-hexiniques substitués par aryloxy-alkylène, procédé de production et utilisation comme médicament
WO2012030165A2 (fr) 2010-08-31 2012-03-08 서울대학교산학협력단 Utilisation de la reprogrammation fœtale d'un agoniste des ppar δ
WO2012059818A1 (fr) * 2010-11-05 2012-05-10 Pronova Biopharma Norge As Méthodes de traitement au moyen de composés lipidiques
CN102459142A (zh) * 2009-05-08 2012-05-16 普罗诺瓦生物医药挪威公司 用于治疗与心血管、代谢和炎性疾病领域相关的疾病的多不饱和脂肪酸
WO2013037390A1 (fr) 2011-09-12 2013-03-21 Sanofi Dérivés amides d'acide 6-(4-hydroxyphényl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs de kinase
WO2013045413A1 (fr) 2011-09-27 2013-04-04 Sanofi Dérivés d'amide d'acide 6-(4-hydroxyphényl)-3-alkyl-1h-pyrazolo[3,4-b] pyridine-4-carboxylique utilisés comme inhibiteurs de kinase
US8741966B2 (en) 2007-11-09 2014-06-03 Pronova Biopharma Norge As Lipid compounds for use in cosmetic products, as food supplement or as a medicament
US8759558B2 (en) 2008-07-15 2014-06-24 Pronova Biopharma Norge As Sulphur containing lipids for use as food supplement or as medicament
WO2016173923A1 (fr) 2015-04-28 2016-11-03 Pronova Biopharma Norge As Utilisation d'acides gras structurellement améliorés contenant du soufre pour prévenir et/ou traiter la stéatose hépatique non alcoolique
US10093618B2 (en) 2013-07-24 2018-10-09 Avexxin As Process for the preparation of a polyunsaturated ketone compound
WO2019224602A2 (fr) 2018-05-23 2019-11-28 Northsea Therapeutics B.V. Acides gras structurellement modifiés pour améliorer la régulation glycémique et traiter une maladie intestinale inflammatoire
KR20200075815A (ko) * 2017-10-23 2020-06-26 에피트래커, 인코포레이티드 지방산 유사체 및 대사 증후군 관련 병태 치료에서의 그의 용도
WO2021124272A1 (fr) * 2019-12-19 2021-06-24 Liminal Biosciences Limited Acides carboxyliques contenant un cycloalkyle et leurs utilisations
US11351139B2 (en) 2013-02-28 2022-06-07 Basf As Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same
US11925614B2 (en) 2017-12-06 2024-03-12 Basf As Fatty acid derivatives for treating non-alcoholic steatohepatitis

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201014633D0 (en) 2010-09-02 2010-10-13 Avexxin As Rheumatoid arthritis treatment
KR101390589B1 (ko) * 2012-05-30 2014-04-30 가천대학교 산학협력단 다이아민을 포함하는 당뇨병의 예방 또는 치료용 조성물
GB201501144D0 (en) * 2015-01-23 2015-03-11 Avexxin As Process for the preparation of a polyunsaturated ketone compound
GB201604316D0 (en) 2016-03-14 2016-04-27 Avexxin As Combination therapy
CA3037582A1 (fr) 2016-09-21 2018-03-29 Avexxin As Composition pharmaceutique
JP7492459B2 (ja) * 2018-05-16 2024-05-29 エピトラッカー インコーポレイテッド 加齢に関連する状態の診断及び治療のための組成物及び方法
EP3796976A4 (fr) 2018-05-23 2022-03-30 Epitracker, Inc. Compositions et méthodes pour le diagnostic et le traitement d'affections liées à la longévité et à la qualité du vieillissement
EP3908374A4 (fr) 2019-01-09 2022-12-28 Epitracker, Inc. Compositions et méthodes pour le diagnostic et le traitement de maladies neurodégénératives
JP7404382B2 (ja) 2019-03-04 2023-12-25 エピトラッカー インコーポレイテッド 脂肪酸アナログ、ならびに認知機能障害、行動症状および慢性疼痛の処置におけるそれらの使用
US20220249525A1 (en) * 2019-05-20 2022-08-11 T Omega As Fatty Acid Compounds for Prevention and Treatment of Neurodegenerative Disorders
US12370166B2 (en) 2021-11-03 2025-07-29 Epitracker, Inc. Pentadecanoylcarnitine for treatment of conditions related to the quality of aging and longevity

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4286053A (en) * 1978-11-24 1981-08-25 Konishiroku Photo Industry Co., Ltd. Process for forming dye images
EP0399183A1 (fr) * 1989-04-07 1990-11-28 Eastman Kodak Company Matériau d'enregistrement photographique avec coupleur formant de colorant bleu-vert
JPH0451149A (ja) * 1990-06-19 1992-02-19 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
US5990173A (en) * 1995-11-28 1999-11-23 Pierre Fabre Medicament 2,3,5-trimethyl-4-hydroxyanilide derivatives, preparation thereof and therapeutical use thereof
US6511670B1 (en) * 1999-04-15 2003-01-28 Societe L'oreal S.A. (poly)thiaalkynoic compounds and pharmaceutical/cosmetic compositions comprised thereof
US20060247458A1 (en) * 2003-02-28 2006-11-02 Shogo Yamamoto Process for the production of optically active compounds having substituents at the 2-position
WO2006117668A1 (fr) 2005-05-04 2006-11-09 Pronova Biopharma Norge As Analogues d'acides gras, autrement dit derives dha utilises comme medicament
WO2008053331A1 (fr) * 2006-11-01 2008-05-08 Pronova Biopharma Norge A/S Lipides oméga-3 à substitution alpha en tant qu'activateurs ou modulateurs du récepteur activé par proliférateurs de peroxisome (ppar)
CN101225064A (zh) * 2007-01-19 2008-07-23 上海汇瑞生物科技有限公司 一种制备β-硫杂-α-烷基脂肪酸的新方法
WO2009061208A1 (fr) * 2007-11-09 2009-05-14 Pronova Biopharma Norge As Composés lipidiques à utiliser dans des produits cosmétiques, en tant que suppléments alimentaires ou en tant que médicaments

Family Cites Families (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2909554A (en) * 1956-07-23 1959-10-20 Monsanto Chemicals Process for the manufacture of (alkylmercapto) alkyl sulfates
GB1038723A (fr) 1962-03-26
JPS4839001B1 (fr) * 1970-11-09 1973-11-21
US4040781A (en) * 1974-06-06 1977-08-09 Lever Brothers Company Novel 2-(alkylsulfinyl)ethyl sulfates and compositions employing same
US4032564A (en) * 1974-09-09 1977-06-28 Zoecon Corporation Esters of cyclopropylalkanols
GB1523276A (en) 1974-09-20 1978-08-31 Lafon Labor Sulphur-containing amino compounds
US4009211A (en) * 1975-07-29 1977-02-22 Gulf Research & Development Company Beta,beta-dialkylethylmercaptoethoxylate as new compounds
US4209410A (en) * 1976-04-28 1980-06-24 Phillips Petroleum Company Lubricants
EP0002007B1 (fr) * 1977-11-11 1982-07-28 Ciba-Geigy Ag Dérivés d'esters de diacides de pyridine, leurs mélanges avec des agents stabilisants métalliques et leur emploi comme agents stabilisants de thermoplastes chlorés
US4368190A (en) * 1980-04-17 1983-01-11 Merck & Co., Inc. Immunologically active dipeptidyl 4-O-,6-O-acyl-2-amino-2-deoxy-D-glucose derivatives and methods for their preparation
DE3164332D1 (en) 1980-10-21 1984-07-26 Boehringer Mannheim Gmbh Phospholipids that contain sulphur, process for their preparation and medicines containing these compounds
US4411808A (en) * 1982-08-04 1983-10-25 Exxon Research & Engineering Co. Multifunctional additive for power transmission shift fluids
US4775223A (en) 1984-09-20 1988-10-04 Canon Kabushiki Kaisha Lactic acid derivative, liquid crystal composition containing same and liquid crystal device
FR2663928B1 (fr) 1990-06-27 1994-04-08 Norsolor Nouveaux composes acryliques soufres, un procede pour leur preparation et leur application a la synthese de nouveaux polymeres.
JPH0543529A (ja) * 1991-08-10 1993-02-23 Taisho Pharmaceut Co Ltd アルカンアミドアンモニウム化合物
US5328952A (en) * 1992-02-14 1994-07-12 Rohm And Haas Company Multi-stage polymer latex cement modifier and process of making
JP2755279B2 (ja) * 1992-03-19 1998-05-20 三井化学株式会社 熱可塑性樹脂組成物およびその成形体
JP2793458B2 (ja) * 1992-03-19 1998-09-03 三井化学株式会社 コネクター用ポリアミド系樹脂組成物およびコネクター
AU7044894A (en) * 1993-06-10 1995-01-03 University Of North Carolina At Chapel Hill, The (phospho)lipids for combatting hepatitis b virus infection
JP3110918B2 (ja) * 1993-06-18 2000-11-20 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
DK70295A (da) * 1994-07-01 1996-01-02 Ciba Geigy Ag Titan- og zirkonium-komplekser af carboxylsyrer som korrosionsinhibitorer
ATE210640T1 (de) * 1994-10-13 2001-12-15 Peptide Technology Ltd Modifizierte mehrfach ungesättigte fettsäuren
US7517858B1 (en) * 1995-06-07 2009-04-14 The Regents Of The University Of California Prodrugs of pharmaceuticals with improved bioavailability
US6262119B1 (en) 1996-04-12 2001-07-17 Peptide Technology Limited Methods of treating immunopathologies using polyunsaturated fatty acids
US6060515A (en) * 1997-01-24 2000-05-09 The Regents Of The University Of California Treatment of skin conditions by use of PPARα activators
WO1999058120A1 (fr) * 1998-05-08 1999-11-18 Rolf Berge Utilisation d'analogues d'acides gras non beta-oxydables pour traiter les etats lies au syndrome x
FR2786187B1 (fr) * 1998-11-19 2001-11-09 Univ Paris Curie Composes du type 2-acylamino-2-deoxy-glucono-1,5-lactone, procede d'obtention, compositions les comportant et utilisations
US6723717B1 (en) * 1999-06-01 2004-04-20 The University Of Texas Southwestern Medical Center Sulfur-containing thyroxane derivatives and their use as hair growth promotors
AU3507600A (en) 1999-06-01 2000-12-18 University Of Texas Southwestern Medical Center, The Substituted biaryl ether compounds
NO328803B1 (no) * 2000-03-03 2010-05-18 Thia Medica Nye fettsyreanaloger
UA75083C2 (uk) 2000-06-22 2006-03-15 Тераванс, Інк. Похідні глікопептидфосфонатів
FR2828487B1 (fr) 2001-08-09 2005-05-27 Genfit S A Nouveaux composes derives d'acides gras, preparation et utilisations
US20030147814A1 (en) * 2001-12-21 2003-08-07 3M Innovative Properties Company Medicinal aerosol formulations comprising ion pair complexes
GB2383355A (en) * 2001-12-22 2003-06-25 Schlumberger Holdings An aqueous viscoelastic fluid containing hydrophobically modified polymer and viscoelastic surfactant
AU2003206762C1 (en) * 2002-01-31 2009-01-15 Tfl Ledertechnik Gmbh Compositions and its use for imparting water repellency to leather or furskins, textiles and other fibrous materials
EP1551228B1 (fr) * 2002-06-13 2012-10-03 New York University C-glycolipide de synthese et utilisation de celui-ci pour le traitement du cancer, des maladies infectieuses et des maladies auto-immunes
KR20050061400A (ko) 2002-06-20 2005-06-22 아이씨 벡 리미티드 황-함유 인지질 유도체
FR2845991B1 (fr) * 2002-10-16 2005-02-04 Pf Medicament Derives d'alpha-phenyl acetanilides et leur application en therapeutique humaine
US8372430B2 (en) * 2002-12-17 2013-02-12 The Procter & Gamble Company Compositions, methods, and kits useful for the alleviation of gastrointestinal effects
DE10326303A1 (de) * 2003-06-11 2004-12-30 Celares Gmbh Reagenzien zur Modifikation von Biopharmazeutika, deren Herstellung und Anwendung
CA2554735A1 (fr) 2004-01-30 2005-08-11 Peplin Biolipids Pty Ltd Molecules porteuses et therapeutiques
JP4563114B2 (ja) 2004-08-30 2010-10-13 出光興産株式会社 潤滑剤用添加剤
EP1856213A2 (fr) 2005-03-08 2007-11-21 CIBA SPECIALTY CHEMICALS HOLDING INC. Patent Departement Particules nanométriques d'oxydes de métaux recouvert avec des n-acylaminomethylene phosphonates spéciaux
EP2004169B1 (fr) 2006-04-12 2012-08-08 Unilever PLC Composition orale comprenant un acide gras polyinsaturé et de l'acide salicylique destinée à produire un effet anti-inflammatoire dans la peau
EP1849449A1 (fr) * 2006-04-26 2007-10-31 3M Innovative Properties Company Composition contenant de la charge et precédé de fabrication et d'utilisation correspondants
US7763607B2 (en) * 2006-04-27 2010-07-27 Solvay Pharmaceuticals Gmbh Pharmaceutical compositions comprising CBx cannabinoid receptor modulators and potassium channel modulators
AU2007249827A1 (en) * 2006-05-09 2007-11-22 Colorado State University Research Foundation Methods for treating blood disorders
WO2008053340A1 (fr) * 2006-11-03 2008-05-08 Pronova Biopharma Norge As Produit de combinaison comprenant au moins un lipide substitué en position alpha et au moins un agent hypoglycémique
DE102007017179A1 (de) 2007-04-12 2008-10-23 Clariant International Ltd. Verfahren zur Herstellung von Alkylpolyglykolcarbonsäuren und Polyglykoldicarbonsäuren mittels Direktoxidation
WO2009149496A1 (fr) 2008-06-10 2009-12-17 Central Northern Adelaide Health Service Traitement du diabète, de ses complications et de troubles associés
FR2933006B1 (fr) 2008-06-27 2010-08-20 Inst Francais Du Petrole Solution absorbante contenant un inhibiteur de degradation soufre a groupement carboxyle et methode pour limiter la degradation d'une solution absorbante
AU2009268610C1 (en) 2008-07-08 2016-02-18 Catabasis Pharmaceuticals, Inc. Fatty Acid Acetylated Salicylates and their uses
EP2147910A1 (fr) 2008-07-15 2010-01-27 Pronova BioPharma Norge AS Nouveaux composés lipidiques
CN102459142B (zh) * 2009-05-08 2017-08-08 普罗诺瓦生物医药挪威公司 用于治疗与心血管、代谢和炎性疾病领域相关的疾病的多不饱和脂肪酸
EP2473045B1 (fr) * 2009-09-01 2016-08-17 Catabasis Pharmaceuticals, Inc. Conjugués acides gras niacine et leurs utilisations
EP2526084A1 (fr) * 2010-01-20 2012-11-28 Pronova BioPharma Norge AS Dérivés salicylates acide gras
EA028535B1 (ru) 2010-11-05 2017-11-30 Пронова Биофарма Норге Ас Способы лечения с применением липидных соединений
WO2012115695A1 (fr) 2011-02-25 2012-08-30 Catabasis Pharmaceuticals, Inc. Conjugués de bis-acides gras et leurs utilisations
WO2013016531A2 (fr) 2011-07-26 2013-01-31 Purdue Research Foundation Composés et méthodes de traitement d'une néoplasie ou d'un cancer

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4286053A (en) * 1978-11-24 1981-08-25 Konishiroku Photo Industry Co., Ltd. Process for forming dye images
EP0399183A1 (fr) * 1989-04-07 1990-11-28 Eastman Kodak Company Matériau d'enregistrement photographique avec coupleur formant de colorant bleu-vert
JPH0451149A (ja) * 1990-06-19 1992-02-19 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
US5990173A (en) * 1995-11-28 1999-11-23 Pierre Fabre Medicament 2,3,5-trimethyl-4-hydroxyanilide derivatives, preparation thereof and therapeutical use thereof
US6511670B1 (en) * 1999-04-15 2003-01-28 Societe L'oreal S.A. (poly)thiaalkynoic compounds and pharmaceutical/cosmetic compositions comprised thereof
US20060247458A1 (en) * 2003-02-28 2006-11-02 Shogo Yamamoto Process for the production of optically active compounds having substituents at the 2-position
WO2006117668A1 (fr) 2005-05-04 2006-11-09 Pronova Biopharma Norge As Analogues d'acides gras, autrement dit derives dha utilises comme medicament
WO2006117664A1 (fr) 2005-05-04 2006-11-09 Pronova Biopharma Norge As Nouveaux derives de dha et utilisation de ceux ci en tant que medicaments
WO2008053331A1 (fr) * 2006-11-01 2008-05-08 Pronova Biopharma Norge A/S Lipides oméga-3 à substitution alpha en tant qu'activateurs ou modulateurs du récepteur activé par proliférateurs de peroxisome (ppar)
CN101225064A (zh) * 2007-01-19 2008-07-23 上海汇瑞生物科技有限公司 一种制备β-硫杂-α-烷基脂肪酸的新方法
WO2009061208A1 (fr) * 2007-11-09 2009-05-14 Pronova Biopharma Norge As Composés lipidiques à utiliser dans des produits cosmétiques, en tant que suppléments alimentaires ou en tant que médicaments

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
FLOCK ET AL., ACTA CHEMICA SCAND., vol. 53, 1999, pages 436
HOLMEIDE ET AL., J.CHEM. SOC., PERKIN TRANS., vol. 1, 2000, pages 2271
JONES, P. B. ET AL: "A New Class of Antituberculosis Agents", J. MED. CHEM., vol. 43, 2000, pages 3304 - 3314, XP002519730 *
LAMANGO, N. S. ET AL: "Inhibition mechanism of S-adenosylmethionine-induced movement deficits by prenylcysteine analogs", PHARMACOLOGY, BIOCHEMISTRY AND BEHAVIOR, vol. 76, 2003, pages 433 - 442, XP002519577 *
LARSEN, L.N. ET AL: "Sulfur-substituted and alpha-methylated Fatty Acids as Peroxisome Proliferator-Activated Receptor Activators", LIPIDS, vol. 40, no. 1, 2005, pages 49 - 57, XP003000338 *
See also references of EP2313090A4
VAAGENES, H. ET AL: "Methylated Eicosapentaenoic Acid and Tetradecylthioacetic Acid: Effects on Fatty Acid Metabolism", BIOCHEMICAL PHARMACOLOGY, vol. 58, 1999, pages 1133 - 1143, XP003000339 *
WILLUMSEN ET AL., J. LIPID MEDIATORS CELL SIGNALLING, vol. 17, 1997, pages 115

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8741966B2 (en) 2007-11-09 2014-06-03 Pronova Biopharma Norge As Lipid compounds for use in cosmetic products, as food supplement or as a medicament
US8759558B2 (en) 2008-07-15 2014-06-24 Pronova Biopharma Norge As Sulphur containing lipids for use as food supplement or as medicament
CN102459142A (zh) * 2009-05-08 2012-05-16 普罗诺瓦生物医药挪威公司 用于治疗与心血管、代谢和炎性疾病领域相关的疾病的多不饱和脂肪酸
US8735436B2 (en) 2009-05-08 2014-05-27 Pronova Biopharma Norge As Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas
US9567280B2 (en) 2010-05-21 2017-02-14 Millercoors Llc Preparation of hop acids and their derivatives
US8871978B2 (en) 2010-05-21 2014-10-28 Millercoors Llc Preparation of hop acids and their derivatives
WO2011146873A1 (fr) * 2010-05-21 2011-11-24 Miller Brewing International, Inc. Préparation d'acides de houblon et de leurs dérivés
WO2011161030A1 (fr) 2010-06-21 2011-12-29 Sanofi Dérivés de méthoxyphényle à substitution hétérocyclique par un groupe oxo, leur procédé de production et leur utilisation comme modulateurs du récepteur gpr40
WO2012004269A1 (fr) 2010-07-05 2012-01-12 Sanofi Dérivés d'acide ( 2 -aryloxy -acétylamino) - phényl - propionique, procédé de production et utilisation comme médicament
WO2012004270A1 (fr) 2010-07-05 2012-01-12 Sanofi Dérivés 1,3-propanedioxyde à substitution spirocyclique, procédé de préparation et utilisation comme médicament
WO2012010413A1 (fr) 2010-07-05 2012-01-26 Sanofi Acides hydroxy-phényl-hexiniques substitués par aryloxy-alkylène, procédé de production et utilisation comme médicament
WO2012030165A2 (fr) 2010-08-31 2012-03-08 서울대학교산학협력단 Utilisation de la reprogrammation fœtale d'un agoniste des ppar δ
CN103347508A (zh) * 2010-11-05 2013-10-09 普罗诺瓦生物医药挪威公司 使用脂质化合物的治疗方法
KR20190072661A (ko) * 2010-11-05 2019-06-25 프로노바 바이오파마 너지 에이에스 지질 화합물을 이용한 치료방법
US9394228B2 (en) 2010-11-05 2016-07-19 Pronova Biopharma Norge As Methods of treatment using lipid compounds
AU2011324909B2 (en) * 2010-11-05 2016-09-08 Pronova Biopharma Norge As Methods of treatment using lipid compounds
KR102265409B1 (ko) 2010-11-05 2021-06-16 바스프 에이에스 지질 화합물을 이용한 치료방법
WO2012059818A1 (fr) * 2010-11-05 2012-05-10 Pronova Biopharma Norge As Méthodes de traitement au moyen de composés lipidiques
TWI578984B (zh) * 2010-11-05 2017-04-21 普諾華生物製藥諾治股份有限公司 使用油脂化合物類之治療方法
EA028535B1 (ru) * 2010-11-05 2017-11-30 Пронова Биофарма Норге Ас Способы лечения с применением липидных соединений
CN107496395A (zh) * 2010-11-05 2017-12-22 普罗诺瓦生物医药挪威公司 使用脂质化合物的治疗方法
WO2013037390A1 (fr) 2011-09-12 2013-03-21 Sanofi Dérivés amides d'acide 6-(4-hydroxyphényl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs de kinase
WO2013045413A1 (fr) 2011-09-27 2013-04-04 Sanofi Dérivés d'amide d'acide 6-(4-hydroxyphényl)-3-alkyl-1h-pyrazolo[3,4-b] pyridine-4-carboxylique utilisés comme inhibiteurs de kinase
US11351139B2 (en) 2013-02-28 2022-06-07 Basf As Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same
US10093618B2 (en) 2013-07-24 2018-10-09 Avexxin As Process for the preparation of a polyunsaturated ketone compound
US10722481B2 (en) 2015-04-28 2020-07-28 Basf As Substituted fatty acids for treating non-alcoholic steatohepatitis
AU2016256552B2 (en) * 2015-04-28 2021-04-01 Pronova Biopharma Norge As Use of structurally enhanced fatty acids containing sulphur for preventing and/or treating non-alcoholic steatohepatitis
WO2016173923A1 (fr) 2015-04-28 2016-11-03 Pronova Biopharma Norge As Utilisation d'acides gras structurellement améliorés contenant du soufre pour prévenir et/ou traiter la stéatose hépatique non alcoolique
US11234948B2 (en) 2015-04-28 2022-02-01 Basf As Substituted fatty acids for treating non-alcoholic steatohepatitis
US11911354B2 (en) 2015-04-28 2024-02-27 Basf Substituted fatty acids for treating non-alcoholic steatohepatitis
US12465580B2 (en) 2015-04-28 2025-11-11 Basf As Substituted fatty acids for treating non-alcoholic steatohepatitis
KR20200075815A (ko) * 2017-10-23 2020-06-26 에피트래커, 인코포레이티드 지방산 유사체 및 대사 증후군 관련 병태 치료에서의 그의 용도
EP3661600A4 (fr) * 2017-10-23 2021-08-11 Epitracker, Inc. Analogues d'acides gras et leur utilisation dans le traitement des états liés au syndrome métabolique
KR102701244B1 (ko) 2017-10-23 2024-09-02 에피트래커, 인코포레이티드 지방산 유사체 및 대사 증후군 관련 병태 치료에서의 그의 용도
US11925614B2 (en) 2017-12-06 2024-03-12 Basf As Fatty acid derivatives for treating non-alcoholic steatohepatitis
US12440466B2 (en) 2017-12-06 2025-10-14 Basf As Fatty acid derivatives for treating non-alcoholic steatohepatitis
WO2019224602A2 (fr) 2018-05-23 2019-11-28 Northsea Therapeutics B.V. Acides gras structurellement modifiés pour améliorer la régulation glycémique et traiter une maladie intestinale inflammatoire
WO2021124272A1 (fr) * 2019-12-19 2021-06-24 Liminal Biosciences Limited Acides carboxyliques contenant un cycloalkyle et leurs utilisations

Also Published As

Publication number Publication date
MY153620A (en) 2015-02-27
AU2009271791A2 (en) 2011-02-24
EP2313090A4 (fr) 2012-01-18
IL210673A0 (en) 2011-03-31
US20110190395A1 (en) 2011-08-04
BRPI0916456B1 (pt) 2020-12-29
US20170029368A1 (en) 2017-02-02
MA33083B1 (fr) 2012-03-01
DK2313090T3 (en) 2016-06-13
EP2313090A1 (fr) 2011-04-27
CO6341548A2 (es) 2011-11-21
EP2313090B1 (fr) 2016-03-30
ES2573977T3 (es) 2016-06-13
CN102159200A (zh) 2011-08-17
VN28144A1 (en) 2011-12-26
IL210673A (en) 2015-02-26
CA2730958A1 (fr) 2010-01-21
PL2313090T3 (pl) 2016-09-30
HUE029195T2 (en) 2017-02-28
ZA201100666B (en) 2011-10-26
NZ601501A (en) 2014-03-28
UA109252C2 (uk) 2015-08-10
CN102159200B (zh) 2015-06-24
US20140316002A1 (en) 2014-10-23
BRPI0916456A2 (pt) 2018-06-12
KR20170093253A (ko) 2017-08-14
NZ590645A (en) 2012-08-31
KR20110031497A (ko) 2011-03-28
JP2011528350A (ja) 2011-11-17
CA2730958C (fr) 2016-07-05
EA022593B1 (ru) 2016-01-29
CL2011000090A1 (es) 2012-03-30
IN2011CH01039A (fr) 2011-12-30
HRP20160557T1 (hr) 2016-06-17
US8759558B2 (en) 2014-06-24
JP5628164B2 (ja) 2014-11-19
BRPI0916456B8 (pt) 2021-05-25
PH12011500113A1 (en) 2010-01-21
AU2009271791A1 (en) 2010-01-21
EP2147910A1 (fr) 2010-01-27
CL2018001111A1 (es) 2018-07-20
MX2011000556A (es) 2011-03-15
SG192525A1 (en) 2013-08-30
EA201170193A1 (ru) 2011-08-30
KR101901836B1 (ko) 2018-09-27
AU2009271791B2 (en) 2014-06-26
HK1161078A1 (en) 2012-08-24

Similar Documents

Publication Publication Date Title
CA2730958C (fr) Nouveaux lipides contenant du soufre pour utilisation en tant que supplement alimentaire ou medicament
TWI558395B (zh) 新穎的脂質化合物
US7550613B2 (en) Compounds
US20100267828A1 (en) dha derivatives and their use as medicaments
EP2248798A1 (fr) Nouveaux composés de lipides
HK1161078B (en) Novel sulphur containing lipids for use as food supplement or as medicament
RU2507193C2 (ru) Альфа-замещенные омега-3 липиды, которые являются активаторами или модуляторами рецептора, активируемого пролифераторами пероксисом (ppar)
AU2013205154A1 (en) Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas
HK1170722B (en) Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200980136136.2

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09798181

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2011518677

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 2011000090

Country of ref document: CL

Ref document number: MX/A/2011/000556

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 2011010093

Country of ref document: EG

ENP Entry into the national phase

Ref document number: 2730958

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 12011500113

Country of ref document: PH

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 590645

Country of ref document: NZ

WWE Wipo information: entry into national phase

Ref document number: 2009271791

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 11016595

Country of ref document: CO

Ref document number: 2009798181

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 20117003422

Country of ref document: KR

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 1039/CHENP/2011

Country of ref document: IN

Ref document number: 201170193

Country of ref document: EA

ENP Entry into the national phase

Ref document number: 2009271791

Country of ref document: AU

Date of ref document: 20090713

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 13054212

Country of ref document: US

ENP Entry into the national phase

Ref document number: PI0916456

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20110114